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WO2000033793A1 - Composition dentaire - Google Patents

Composition dentaire Download PDF

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Publication number
WO2000033793A1
WO2000033793A1 PCT/US1999/029367 US9929367W WO0033793A1 WO 2000033793 A1 WO2000033793 A1 WO 2000033793A1 US 9929367 W US9929367 W US 9929367W WO 0033793 A1 WO0033793 A1 WO 0033793A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
unsubstituted
alkylene
denotes
heteroarylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1999/029367
Other languages
English (en)
Inventor
Joachim E. Klee
Uwe Walz
Rolf Mulhaupt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dentsply Sirona Inc
Original Assignee
Dentsply International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dentsply International Inc filed Critical Dentsply International Inc
Priority to JP2000586288A priority Critical patent/JP2002531476A/ja
Priority to EP99966119A priority patent/EP1137389A1/fr
Publication of WO2000033793A1 publication Critical patent/WO2000033793A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A61K6/893—Polyurethanes

Definitions

  • a dental composition comprising mono- and/or a polycyanoacrylate, a polymerizable monomer, a stabilizer, an initiator, pigments and a filling material.
  • the invented dental composition is usable as dental filling material, dental cement, dental sealer or as dental adhesive.
  • Dental cements that are available on the market are Zn-phosphate cements, glass ionomer cements, self-curing adhesives on basis of composite resins or a relatively new class of compomer cements. All these cements require a mixing of two components to reach a solid product. Frequently, powder and liquid or two pastes were applied. However, the solidification is a process that is relatively independent of the applicator. That means after mixing the components the process of free-radical polymerization or acid-base reaction takes place.
  • light-curing cements are advantageously, because they polymerize when irradiated with visible light.
  • light polymerizable cements are usable, e.g. for composite or ceramic inlays, onlays or crowns.
  • Metallic and metal fused porcelain restorations are only adherable by using of self-curing cements.
  • an one component self-curing cement should represent an great advantage.
  • This cement should by a command-setting material that is applicable under metallic or highly-opaque materials, too.
  • One possibility to realize this aim is the application of mono- and polycyanoacryaites due to their possibility to polymerized in presence of water and amines or other anionic initiators.
  • the anionic polymerization of cyanoacrylates seemed to be advantageous due to the complete polymerization of the material.
  • a smearlayer comparable to the oxygen inhibited layer of free-radical polymerizations is completely missing. Synthesis and properties of modified cyanoacrylates as well as their anionic polymerization were investigated some years ago (US 3316227; N.N. Trofimov et al. Zh. Vses. Khim. O-va. 19 (1974) 473; Z. Denchev et al., J. Appl. Polym. Sci. 42 (1991 ), 2933).
  • Butylcyanoacrylate is used as a glue for fixation of bone fragments (M.A. Shermak et al., Plast Reconstr Surg 1998 Aug;102 (2):319-24),. Isopropyl cyanoacrylate is applied as root canal cement (E. L. Jacobson et al., J. Endodontics 16 (1990) 516).
  • monocyanoacrylates are limited concerning mechanical stability and due to moisture sensitivity. Furthermore, they are disadvantageous due to solubilty of the linear polymers.
  • a dental composition comprising at least a mono- and/or a polycyanoacrylate, a polymerizable monomer, a stabilizer, an initiator, pigments and a filling material.
  • the mono- and polycyanoacrylates are characterized by the following structure:
  • Z 2 denotes CN, COOR 4 , COR 4 , NO 2 R, denotes hydrogen, or a substituted or unsubstituted C, to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 2 denotes hydrogen, or a substituted or unsubstituted C 1 to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 3 denotes a difunctional substituted or unsubstituted C_ to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 4 denotes hydrogen, or a substituted or unsubstituted C, to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 5 denotes a difunctional substituted or unsubstituted C, to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene,
  • R 6 denotes a substituted or unsubstituted C . to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to
  • R 7 denotes a polyfunctional substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene or heteroarylene, selected from the group
  • the mono- and polycyanoacrylates are characterized by the following structures:
  • R denotes hydrogen, or a substituted or unsubstituted C . to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 2 denotes hydrogen, or a substituted or unsubstituted C 1 to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 3 denotes a difunctional substituted or unsubstituted C, to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 4 denotes hydrogen, or a substituted or unsubstituted C . to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene,
  • R 5 denotes a difunctional substituted or unsubstituted C, to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene,
  • R 5 denotes a substituted or unsubstituted C, to C 18 alkylene, C 5 to C 18 substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to
  • R 7 denotes a polyfunctional substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene or heteroarylene, selected from the group — CH 2 — CH CH 2 -C
  • polymerizable monomers are used mono- and polyfunctional (meth)-acrylates, such as a polyalkylenoxide di- and poly(meth)acrylate, an urethane di- and poly(meth) acrylate, a vinyl-, vinylen- orvinyliden-, acrylate- or methacrylate substituted spiroorthoester, a spiroorthocarbonate or a bicyloorthoester; preferably were used diethylenglycol dimethacrylate, triethylenglycol dimethacrylate, 3,(4),8,(9)-dimethacryloyloxymethyl tricyclo- decane, dioxolan bismethacryiate, glycerol tri methacrylate, furfuryl methacrylate in a content of 5 to 80 wt-%.
  • mono- and polyfunctional (meth)-acrylates such as a polyalkylenoxide di- and poly(meth
  • the polymerization initiator for the dental composition is a thermal initiator or a photoinitiator and/or an anionic polymerization initiator.
  • the polymerization of the invented mono- and polycyanoacrylates is initiated by free-radical and anionic polymerization initiators or only by an anionic polymerization initiator.
  • water acts as anionic polymerization initiator.
  • the well-known Reinecke salt K + Cr(NH 3 ) 2 (NCS) 4 " (C.Kutsl et al, Macromolecules 24 (1991 ) 6872) and group IV metal carbonyl pyridine complexes (R.B. Paul et al. Polymer 38 (1997) 2011 ) are usable as photoinitiators for photoinduced anionic polymerization.
  • the monomers are stabilized by using radical absorbing monomer such as hydrochinon monomethylether, hydrochinondimethylether, BHT.
  • Mono- and polycyanoacrylates are stabilized by using of acids such as phosphoric acid, arylphosphonic acid, SO 2 , p-toluensulfonic acid.
  • the invented dental composition comprises as filing materials inorganic and/or organic fillers.
  • the invented dental composition is usable as dental filling material, dental cement, dental sealer or as dental adhesive.
  • Mono- and polycyanoacrylates are usable in a dental compositions such as in restoratives, adhesives, bases and liners, root canal sealers and for others. Furthermore, the invented mono- and polycyanoacrylates are usable in electronics, microelectronics as industrial adhesives or for medical applications.
  • DEGBCA was prepared according the same procedure described in example 7.
  • Compressive strength of samples that were polymerized after initiation with N,N-Dimethyl benzylamine is 65.9 ⁇ 8.3 MPa.
  • Compressive strength of samples that were polymerized after initiation with N,N-Dimethyl benzylamine is 57.3 ⁇ 6J MPa.
  • Compressive strength of samples that were polymerized for 30 minutes at 60 °c after initiation with Trimethylamine is 46.4 ⁇ 6.3 MPa.

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Dental Preparations (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention concerne une composition dentaire comprenant un monocyanoacrylate et/ou un polycyanoacrylate, un monomère polymérisable, un stabilisant, un initiateur, et éventuellement, des pigments et un matériau d'obturation.
PCT/US1999/029367 1998-12-11 1999-12-10 Composition dentaire Ceased WO2000033793A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000586288A JP2002531476A (ja) 1998-12-11 1999-12-10 歯科用組成物
EP99966119A EP1137389A1 (fr) 1998-12-11 1999-12-10 Composition dentaire

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11186498P 1998-12-11 1998-12-11
US60/111,864 1998-12-11

Publications (1)

Publication Number Publication Date
WO2000033793A1 true WO2000033793A1 (fr) 2000-06-15

Family

ID=22340846

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/029367 Ceased WO2000033793A1 (fr) 1998-12-11 1999-12-10 Composition dentaire

Country Status (4)

Country Link
US (3) US20020025993A1 (fr)
EP (1) EP1137389A1 (fr)
JP (1) JP2002531476A (fr)
WO (1) WO2000033793A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1962713A2 (fr) * 2005-11-25 2008-09-03 Lietzau, Markus Sonde, procédé et kit et leur utilisation pour rendre étanche l'extrémité apicale d'un canal radiculaire dentaire

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7086864B2 (en) 1999-05-12 2006-08-08 Pentron Clinical Technologies, Llc Endodontic post system
US7168952B2 (en) 1999-05-12 2007-01-30 Pentron Clinical Technologies, Llc Endodontic post and obturating system
US7163401B2 (en) 1999-05-12 2007-01-16 Pentron Clinical Technologies, Llc Endodontic post and obturating system
US7750063B2 (en) 2001-10-24 2010-07-06 Pentron Clinical Technologies, Llc Dental filling material
US7204874B2 (en) 2001-10-24 2007-04-17 Pentron Clinical Technologies, Llc Root canal filling material
US7211136B2 (en) 2001-10-24 2007-05-01 Pentron Clinical Technologies, Llc Dental filling material
US7204875B2 (en) 2001-10-24 2007-04-17 Pentron Clinical Technologies, Llc Dental filling material
US7303817B2 (en) 2001-10-24 2007-12-04 Weitao Jia Dental filling material
US6884073B2 (en) * 2002-04-30 2005-04-26 Richard H. Chilibeck Temporary and semi-permanent dental crowns
US7252508B2 (en) 2002-12-13 2007-08-07 Pentron Clinical Technologies, Llc Endodontic obturator
JP4261288B2 (ja) * 2003-08-22 2009-04-30 デンツプライ三金株式会社 歯科用接着剤組成物
DE602005020806D1 (de) * 2004-06-15 2010-06-02 Dentsply Int Inc Mensetzungen mit geringer polymerisationsspannung
JP2008502697A (ja) * 2004-06-15 2008-01-31 デンツプライ インターナショナル インコーポレーテッド 低収縮且つ低応力の歯科用組成物
JP2019178119A (ja) * 2018-03-30 2019-10-17 株式会社ジーシー 歯科用重合性組成物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041062A (en) * 1975-11-18 1977-08-09 Johnson & Johnson Modified cyanoacrylate monomers and methods of preparation
WO1983002450A1 (fr) * 1982-01-18 1983-07-21 Loctite Corp Cyanoacrylates renforces contenant des caoutchoucs elastomeres
JPH0444769A (ja) * 1990-06-11 1992-02-14 Nisshin:Kk 生体硬組織用充填組成物
WO1994015907A1 (fr) * 1993-01-11 1994-07-21 Eurotax Limited Procede pour la preparation d'esters de l'acide 2-cyanacrylique et utilisation des esters ainsi prepares comme adhesifs
US5691113A (en) * 1991-11-12 1997-11-25 The University Of Georgia Research Foundation, Inc. Anionic photoinitiation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3316227A (en) * 1963-10-18 1967-04-25 Lord Corp Preparation of 1, 1-disubstituted diunsaturated compounds
US3940362A (en) * 1972-05-25 1976-02-24 Johnson & Johnson Cross-linked cyanoacrylate adhesive compositions
US4012402A (en) * 1974-10-04 1977-03-15 Johnson & Johnson Modified cyanoacrylate monomers and methods for preparation
US5913840A (en) * 1997-08-15 1999-06-22 Minnesota Mining And Manufacturing Company Soft orthopedic casting article with reinforcement system

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4041062A (en) * 1975-11-18 1977-08-09 Johnson & Johnson Modified cyanoacrylate monomers and methods of preparation
WO1983002450A1 (fr) * 1982-01-18 1983-07-21 Loctite Corp Cyanoacrylates renforces contenant des caoutchoucs elastomeres
JPH0444769A (ja) * 1990-06-11 1992-02-14 Nisshin:Kk 生体硬組織用充填組成物
US5691113A (en) * 1991-11-12 1997-11-25 The University Of Georgia Research Foundation, Inc. Anionic photoinitiation
WO1994015907A1 (fr) * 1993-01-11 1994-07-21 Eurotax Limited Procede pour la preparation d'esters de l'acide 2-cyanacrylique et utilisation des esters ainsi prepares comme adhesifs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 016, no. 219 (C - 0943) 22 May 1992 (1992-05-22) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1962713A2 (fr) * 2005-11-25 2008-09-03 Lietzau, Markus Sonde, procédé et kit et leur utilisation pour rendre étanche l'extrémité apicale d'un canal radiculaire dentaire
US9724173B2 (en) 2005-11-25 2017-08-08 Markus Lietzau Use of bone adhesive for apical sealing a tooth root canal

Also Published As

Publication number Publication date
US20020025993A1 (en) 2002-02-28
JP2002531476A (ja) 2002-09-24
EP1137389A1 (fr) 2001-10-04
US20020147249A1 (en) 2002-10-10
US20050054748A1 (en) 2005-03-10

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